Irbesartan

Irbesartan, sold under the brand name Aprovel among others, is a medication used to treat high blood pressure, heart failure, and diabetic kidney disease.^[4] It is a reasonable initial treatment for high blood pressure.^[4] It is taken by mouth.^[4] Versions are available as the combination irbesartan/hydrochlorothiazide.^[4][5][6][7]

Irbesartan

Clinical data
Pronunciation	/ɜːrbəˈsɑːrtən/
Trade names	Aprovel, Avapro, others
AHFS/Drugs.com	Monograph
MedlinePlus	a698009
License data	US DailyMed: Irbesartan
Pregnancy category	AU: D[1]
Routes of administration	By mouth
Drug class	Cardiovascular agent
ATC code	C09CA04 (WHO) C09DA04 (WHO)
Legal status
Legal status	AU: S4 (Prescription only)[2] UK: POM (Prescription only) US: ℞-only EU: Rx-only[3] In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	60% to 80%
Protein binding	~90%
Metabolism	Liver (CYP2C9)
Elimination half-life	11 h to 15 h
Excretion	Kidney 20%, feces 65%
Identifiers
IUPAC name 2-butyl-3-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1,3-diazaspiro[4.4]non-1-en-4-one
CAS Number	138402-11-6 Y
PubChem CID	3749
IUPHAR/BPS	589
DrugBank	DB01029 Y
ChemSpider	3618 Y
UNII	J0E2756Z7N
KEGG	D00523 Y
ChEBI	CHEBI:5959 Y
ChEMBL	ChEMBL1513 Y
CompTox Dashboard (EPA)	DTXSID0023169
ECHA InfoCard	100.119.966
Chemical and physical data
Formula	C25H28N6O
Molar mass	428.540 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C1N(\C(=N/C12CCCC2)CCCC)Cc5ccc(c3ccccc3c4n[nH]nn4)cc5
InChI InChI=1S/C25H28N6O/c1-2-3-10-22-26-25(15-6-7-16-25)24(32)31(22)17-18-11-13-19(14-12-18)20-8-4-5-9-21(20)23-27-29-30-28-23/h4-5,8-9,11-14H,2-3,6-7,10,15-17H2,1H3,(H,27,28,29,30) Y Key:YOSHYTLCDANDAN-UHFFFAOYSA-N Y
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Mechanism of action

Irbesartan is an angiotensin II receptor antagonist and works by blocking the effects of angiotensin II.^[4]

Medical uses

Irbesartan is used for the treatment of hypertension. It may also delay progression of diabetic nephropathy and is also indicated for the reduction of renal disease progression in patients with type 2 diabetes,^[8] hypertension and microalbuminuria (>30 mg/24 h) or proteinuria (>900 mg/24 h).^[9]

Combination with diuretic

Irbesartan is also available in a fixed-dose combination formulation with hydrochlorothiazide, a thiazide diuretic, to achieve an additive antihypertensive effect.^{[10][11][6][12]}

Side effects

Common side effects include dizziness, diarrhea, feeling tired, muscle pain, and heartburn.^[4][13] Serious side effects may include kidney problems, low blood pressure, and angioedema.^[4] Use in pregnancy may harm the baby and use when breastfeeding is not recommended.^[14]

History

Irbesartan was developed by Sanofi Research (part of Sanofi-Aventis). It is jointly marketed by Sanofi-Aventis and Bristol-Myers Squibb under the brand names Aprovel, Karvea, and Avapro.^[5][1]

It was patented in 1990, and approved for medical use in 1997.^[15] It is available as a generic medication.^[13] In 2022, it was the 200th most commonly prescribed medication in the United States, with more than 2 million prescriptions.^[16][17]

Recalls

See also: Valsartan § recalls, and Angiotensin II receptor blocker § recalls

In 2018, the US Food and Drug Administration (FDA) reported that some versions of the angiotensin II receptor blocker medicines (including valsartan, losartan, irbesartan and other "-sartan" drugs) contain nitrosamine impurities.^[18] Health Canada also reported nitrosamine impurities.^[19]

The FDA issued revised guidelines about nitrosamine impurities in September 2024.^[20]